


First Time Mishaps

by Turtleduck23



Category: Shingeki no Kyojin | Attack on Titan
Genre: Alternate Universe - Modern Setting, Anal Fingering, Anal Sex, Bottom Armin Arlert, Established Relationship, First Time, Fluff, Fluff and Smut, M/M, Painful Sex, Top Jean Kirstein
Language: English
Status: Completed
Published: 2021-02-09
Updated: 2021-02-09
Packaged: 2021-03-15 10:54:38
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,785
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29312910
Author URL: https://archiveofourown.org/users/Turtleduck23/pseuds/Turtleduck23
Summary: Armin and Jean had their first time; Things didn't go as planned
Relationships: Armin Arlert/Jean Kirstein
Comments: 2
Kudos: 35





	First Time Mishaps

**Author's Note:**

> I have no idea what this is. It is my first time writing hdbcjshbcjhscb  
> I'm sorry lmao

They had been dating for 3 months, and slowly getting more and more intimate. It all started with pecks that soon became long make out sessions that escalated to neck kissing; Armin had a thing for neck kissing, not sucking or biting, just gentle neck kissing; it made him feel fluttery, and caused him to gasp quietly and grasp onto Jean’s shirt tightly. When neck kissing wasn’t enough they went on to touch each other through their clothes, rubbing and massaging; fondling all the sensitive areas they could get their hands on. 

During their three months they had gradually grown more comfortable, more curious, which eventually led up to the idea of going all the way. 

Armin was terrified, even though he wanted it almost as much as Jean, he was never good with pain, and some widely known fact had recently gotten into his head is that Having sex for the first time HURT; specially if it’s anal sex. 

Jean was nervous, he had sex before, but never with a man, and the thought of doing it wrong or not being able to satisfy his partner haunted him. He wanted this to be right for both of them, to fondly remember the first time they made love. 

Their afternoon started like any other, Armin had invited Jean over to hang out, maybe order some food and watch a movie. His grandpa had gone to visit one of his friends he hadn’t seen in a while, and was probably gonna take a couple of hours before he came back home. 

“do you wanna order anything?” Jean asked scrolling through the delivery app on his phone, “Not really, I’m not hungry, I had lunch before you arrived; we could order some dinner later tho” Armin said while scooting closer to the taller man. “Let’s check later then” Jean put his phone in Armin’s nightstand and wrapped his arms around the blonde, Armin pulled a light blue blanket over the two of them and rested his head on Jean’s chest.

They stayed like that for a while; enjoying each other’s company, Armin enjoyed listening to his heartbeat, it was soothing. Jean gently caressed his hair, and made sure he was also lightly massaging his scalp, just like his boyfriend liked it. “Jean” he looked up “yes baby?” “can I kiss you?” the smaller man asked, he knew he did not have to, but it had become a habit. After receiving a positive response he leaned to kiss him, opening his mouth slightly almost immediately, he didn’t mean this to be a short peck. 

Their tongues were brushing sweetly against each other, Armin put his leg over Jean’s and pressed his crotch lightly againsts the other’s thigh, he knew he’d enjoy grinding against it later on if things kept escalating. Jean put his hand on the back of his boyfriend’s head and grasped his hair lightly, being careful not to pull too hard but making sure Armin couldn't pull away. 

Jean trailed kisses down Amin’s neck, making the younger boy hold onto the back of his shirt and gasp. They changed positions, with Jean now on top of Armin still kissing down his neck while unbuttoning his shirt, peppering kisses all over his chest. After trailing down to his stomach he paused and pulled away eliciting a whine from Armin. “Do you… you know, want to go further today?” “f-further? y-you mean, all the way?” “yes! only if you’re comfortable with it” He thought about his answer for a moment, he wanted it, and the only way to get rid of his fear was confronting it, so he nodded “you do?” “yeah, I mean, we’re eventually gonna do it, why not now?” 

Jean unzipped his boyfriend’s pants and pulled them down his slim legs, smiling at the view. He then proceeded to take off his own shirt and pants, leaving them both in their underwear. He leaned to kiss armin, while he rubbed their two clothed erections together, making Armin moan and squirm lightly under him. “do you have lube and condoms?” “no… wait, actually, i think there’s a condom in the first drawer of the nightstand, I don’t have any lube tho” “that’ll do, there’s always saliva”.

Armin felt himself blush when Jean pulled his underwear down, pressing his legs together by instinct to try and cover himself a bit. 

Jean pulled his legs apart gently, not wanting to make Armin feel pressured to do anything. He spread his cheeks open and licked lightly making his boyfriend gasp and grab onto the bed sheets. He slowly worked his tongue in; then he replaced it by a finger and Armin tensed. “Shhh, it’s okay, just relax” he said while moving the finger slightly inside him, looking for his prostate. Armin moaned loudly when Jean found it, feeling a jolt of pleasure run down his spine. 

He kept working on it, making sure to pleasure him to distract him from the other finger that wiggled its way inside. It was tight, it burned slightly; saliva dries quickly and they were just starting to notice. Armin pressed his eyes shut and breathed in deeply, the pain wasn’t bad, but he was scared. 

“Armin, baby, relax; you’re tense, it’s gonna hurt more if you clench” He nodded trying to obey and relax, taking a few deep breaths “c-continue”. Jean complied and worked him open, he was worried for him, he knew Armin was having a hard time taking things easy. 

A third finger was inserted, Armin took it in better than the other two, which gave him confidence, it felt good, and Jean was doing a good job hitting his prostate with his fingers “c-could you go a bit faster? It feels good” Jean smiled and did as told. Armin whined when his boyfriend picked up the pace, enjoying the feeling and finally relaxing a bit. “I think I’m ready” “you sure baby? We could keep this up a bit longer” Armin nodded “I want it Jean, please” 

Jean pulled fingers out, then proceeded to take his underwear off. He slipped a condom on and spit on his hand and stroked his dicked, trying to get it coated. “Should I help you, Jean?” Armin said, sitting on the bed “I can.. you know.. s-suck it if you want me to”. They had done it before, quite a couple of times as well, but Armin was still shy about it. 

He took Jean’s dick in his mouth, his objective wasn’t to make him cum, but to coat his dick with saliva. It didn’t take him long, he started by spitting on the tip, and then spreading it all evenly with his tongue. It felt heavenly, having Armin’s mouth all over him making his dick wetter by the second was driving him crazy. Armin let go of his dick, “do you think that’s enough?” “Yes baby, thank you, you did a good job”. Jean pressed Armin down on bed again, then leaned down to kiss his forehead “are you okay?” Armin modded “I’m just nervous” “we can stop” Armin shook his head “I want this” 

Armin’s legs were spread open, Jean positioned himself while peppering Armin’s face with kisses, “I’m gonna do it now, okay? Relax for me” he gently pushed forward, pressing his dick against Armin’s hole. 

He tried to stay calm, he took deep breaths and held Jean tightly against him. It wasn’t going in; Jean kept pushing, trying to be as gentle as possible. Armin repositioned his legs, spreading them a bit more, making his cheeks be further apart. That’s all it took for the tip to go in suddenly.

The pain was there, and it was bad. Armin’s eyes filled with tears and held onto Jean even tighter, letting out a sound of pain. Jean panicked, “did I hurt you?” No response “Armin baby talk to me, do you want me to take it out?” Armin shook his head, that probably was gonna hurt more. “I-it hurts'' his voice was quivering; he was clearly crying. “I’m gonna pull out” “n-no Jean! W-wait, it’s getting better” “Baby, you’re hurting” “it’s gonna hurt m-more if you pull it out” “should I keep going then?” Armin took a second to respond and nodded.

Jean pushed in very slowly, he could feel the crook of his neck getting wet with Armin’s tears, and his back getting pierced by nails desperately clinging onto him “shhh it’s okay, we’re almost there”. When his whole length was inside, he sweetly wiped Armin’s tears “how are you feeling baby?” “I-it hurts a bit less, c-can we stay like this for a bit?” “As long as you need” 

It took a couple of minutes for Armin to calm down and get used to the intrusion “I’m ready, you can.. you can move now” Jean started moving, slow at first, a new wave of pain washed over Armin, making him cling onto Jean again, Jean kept on going, picking up the pace, the pain slowly faded away, and turned into warm pleasure. 

He let go of Jean and closed his eyes, moaning softly, enjoying the feeling “F-fuck, baby you’re so tight. D-does it feel nice?” Armin nodded, moving his hips lightly along Jean’s thrusts. 

Jean grabbed Armin’s hips and positioned them at an angle in order to hit his prostate. As soon as he did Armin’s eyes filled with fresh tears, this time of pleasure “t-there! Jean there!” Jean picked up the pace and thrusted at that same angle with strength. Armin’s eyes rolled to the back of his head and moaned loudly “I-I’m close” Jean grabbed Armin’s dick and stroked it, overstimulating him “f-fuck!” With that he came all over his boyfriend’s hand, and Jean came a few seconds later, collapsing on Armin’s chest. 

“That was nice” said Jean “y-yeah… um… can you pull out please? I’m getting sore” “s-sure, sorry about that” he gently pulled out and Armin gasped, as he expected, it did hurt. 

“Do you wanna take a shower?”

Jean pulled him on bed to sit down, “Do you think you can walk?” “I don’t know, my legs feel funny” he tried to stand and his knees buckled, Jean was quick to loop his arms under his “woah, careful” “s-sorry”.

After a nice long shower Jean dressed Armin in fresh clothes and laid him on bed, Armin had objected, arguing that he could dress himself, but Jean didn’t seem to care. He dressed himself as well and laid next to Armin, pulling him into his arms and kissing his head. “How's your ass?” “In pain, but not as bad as I thought, at some point I believed it was gonna rip me open” Jean chuckled.


End file.
